Glenwood Holidays

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    Save up to €185 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Glenwood

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €1,303, price is now €843 per person
€843
per person
2 Nov - 9 Nov
found 17 hours ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Friendly staff, clean and comfortable, convenient location

Reviewed on 20 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €2,651, price is now €1,575 per person
€1,575
per person
2 Nov - 9 Nov
found 17 hours ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €2,018, price is now €1,253 per person
€1,253
per person
2 Nov - 9 Nov
found 17 hours ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable

Reviewed on 17 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,413, price is now €924 per person
€924
per person
2 Nov - 9 Nov
found 17 hours ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9/10 Wonderful! (335 reviews)
Great except parking

Reviewed on 19 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,879, price is now €1,239 per person
€1,239
per person
2 Nov - 9 Nov
found 17 hours ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug 2025

Top hotels in Glenwood

Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
The price is €125 per night from 27 Aug to 28 Aug
€125
27 Aug - 28 Aug
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"It was safe and shopping and food were excellent nearby; there were some outside renovations being done but overall it was great."

Reviewed on 19 Aug 2025

Hilton Chicago/Oak Lawn
Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
6540 S Cicero Ave, Chicago, IL
The price is €136 per night from 2 Sept to 3 Sept
€136
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,148 reviews)
Greg Coleman
"The surprise $30 a day parking fee. Should have been mentioned when I booked"

Reviewed on 16 Aug 2025

Hampton Inn by Hilton Chicago-Midway Airport
Motel 6 Bridgeview, IL

Motel 6 Bridgeview, IL

2 out of 5
9625 S 76th Ave, Bridgeview, IL
Fully refundableReserve now, pay when you stay
The price is €47 per night from 24 Aug to 25 Aug
€47
24 Aug - 25 Aug
includes taxes & fees
6.8/10 (1,201 reviews)
"Absolutely awesome"

Reviewed on 17 Aug 2025

Motel 6 Bridgeview, IL
See all 899 properties in Glenwood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Glenwood holiday package cost?
You can pick up a holiday package to this top destination from €843 on Expedia. But how much your holiday to Glenwood costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Glenwood?
January, February and November are great times to look for cheap Glenwood holiday packages. Choosing to travel in quieter months means you can typically find reduced prices on hotels and flights.
How many days is enough for Glenwood?
With a well-planned itinerary, you can easily visit the main Glenwood sights in a handful of days. But if you'd like to discover lesser-known spots or go on day trips, consider booking your Glenwood holiday for longer.
How to find the best Glenwood package deals?
Use Expedia's filters to help you find some of the best Glenwood package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Glenwood package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Glenwood holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Glenwood holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Glenwood?
If you've got your Glenwood holiday dates finalized, book early to snap up some awesome deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
How to plan a trip to Glenwood?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Glenwood.
  2. Set a budget: Factor in costs such as flights, food and transportation when calculating how much to put aside for your trip to Glenwood. Then, choose a hotel that fits your budget, whether that's a low-cost option or a deluxe retreat.
  3. Decide how many days away: Start by compiling a list of the activities and attractions you'd like to experience in Glenwood. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Glenwood holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.